DE1263781B - Verfahren zur Herstellung von 2-Methoxy-3, 6-dichlorbenzoesaeure - Google Patents
Verfahren zur Herstellung von 2-Methoxy-3, 6-dichlorbenzoesaeureInfo
- Publication number
- DE1263781B DE1263781B DEV28543A DEV0028543A DE1263781B DE 1263781 B DE1263781 B DE 1263781B DE V28543 A DEV28543 A DE V28543A DE V0028543 A DEV0028543 A DE V0028543A DE 1263781 B DE1263781 B DE 1263781B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- reaction
- methoxy
- dichlorobenzoic acid
- pressure
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229940050176 methyl chloride Drugs 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- FKIKPQHMWFZFEB-UHFFFAOYSA-N 3,6-dichloro-2-hydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C(Cl)=CC=C1Cl FKIKPQHMWFZFEB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 3
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- QVTQYSFCFOGITD-UHFFFAOYSA-N 2,5-dichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1Cl QVTQYSFCFOGITD-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 235000005985 organic acids Nutrition 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 claims 1
- YDOVRFJDZXIYMW-UHFFFAOYSA-N 3,4-dichloro-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(Cl)=C1O YDOVRFJDZXIYMW-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229910000831 Steel Inorganic materials 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 238000005119 centrifugation Methods 0.000 claims 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 238000005259 measurement Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 229910001220 stainless steel Inorganic materials 0.000 claims 1
- 239000010935 stainless steel Substances 0.000 claims 1
- 239000010959 steel Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000012546 transfer Methods 0.000 claims 1
- 238000009423 ventilation Methods 0.000 claims 1
- 238000013022 venting Methods 0.000 claims 1
- 239000002585 base Substances 0.000 description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- 239000012022 methylating agents Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- AWSBKDYHGOOSML-UHFFFAOYSA-N dicamba-methyl Chemical compound COC(=O)C1=C(Cl)C=CC(Cl)=C1OC AWSBKDYHGOOSML-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/02—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by the reacting monomers or modifying agents during the preparation or modification of macromolecules
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US371077A US3335177A (en) | 1964-05-28 | 1964-05-28 | Process for preparing 2-methoxy-3, 6-dichlorobenzoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1263781B true DE1263781B (de) | 1968-03-21 |
Family
ID=23462381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEV28543A Pending DE1263781B (de) | 1964-05-28 | 1965-05-24 | Verfahren zur Herstellung von 2-Methoxy-3, 6-dichlorbenzoesaeure |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3335177A (xx) |
| JP (1) | JPS5127667B1 (xx) |
| BE (1) | BE664536A (xx) |
| CH (1) | CH482641A (xx) |
| DE (1) | DE1263781B (xx) |
| DK (1) | DK112875B (xx) |
| ES (1) | ES313423A1 (xx) |
| FR (1) | FR1440940A (xx) |
| GB (1) | GB1038605A (xx) |
| IL (1) | IL23485A (xx) |
| LU (1) | LU48692A1 (xx) |
| NL (1) | NL6506607A (xx) |
| SE (1) | SE326198B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969404A (en) * | 1973-06-22 | 1976-07-13 | Celamerck Gmbh & Co. Kg | Process for preparation of 2-methoxy-3,6-dichloro-benzoic acid |
| WO2018106564A1 (en) * | 2016-12-07 | 2018-06-14 | Monsanto Technology Llc | Processes for purification, recovery, and conversion of chlorophenol salts and preparation and recovery of products prepared therefrom |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1801901A (en) * | 1927-08-26 | 1931-04-21 | Dow Chemical Co | Method of making phenol ethyl ethers |
| US2240034A (en) * | 1937-05-19 | 1941-04-29 | Harvel Corp | Ethers of cashew nut sheell liquid and process of making them |
| US3013054A (en) * | 1958-08-04 | 1961-12-12 | Velsicol Chemical Corp | 2-methoxy-3, 6-dichlorobenzoates |
-
1964
- 1964-05-28 US US371077A patent/US3335177A/en not_active Expired - Lifetime
-
1965
- 1965-05-05 GB GB19043/65A patent/GB1038605A/en not_active Expired
- 1965-05-05 IL IL23485A patent/IL23485A/xx unknown
- 1965-05-21 FR FR17888A patent/FR1440940A/fr not_active Expired
- 1965-05-24 DE DEV28543A patent/DE1263781B/de active Pending
- 1965-05-25 NL NL6506607A patent/NL6506607A/xx unknown
- 1965-05-26 CH CH735765A patent/CH482641A/de not_active IP Right Cessation
- 1965-05-26 LU LU48692D patent/LU48692A1/xx unknown
- 1965-05-26 DK DK267665AA patent/DK112875B/da unknown
- 1965-05-26 ES ES0313423A patent/ES313423A1/es not_active Expired
- 1965-05-26 BE BE664536A patent/BE664536A/xx unknown
- 1965-05-28 SE SE07041/65A patent/SE326198B/xx unknown
- 1965-05-28 JP JP40031184A patent/JPS5127667B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES313423A1 (es) | 1966-02-16 |
| SE326198B (xx) | 1970-07-20 |
| BE664536A (xx) | 1965-11-26 |
| IL23485A (en) | 1969-07-30 |
| US3335177A (en) | 1967-08-08 |
| FR1440940A (fr) | 1966-06-03 |
| GB1038605A (en) | 1966-08-10 |
| CH482641A (de) | 1969-12-15 |
| JPS5127667B1 (xx) | 1976-08-13 |
| LU48692A1 (xx) | 1965-11-26 |
| NL6506607A (xx) | 1965-11-29 |
| DK112875B (da) | 1969-01-27 |
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